Six Degrees of Loving Blair Waldorf
by Chair4vr
Summary: A look into the past and present feelings of the men of the Upper East Side regarding Blair Waldorf.
1. Chapter 1

_So this is just something that came to me today. I hope you guys like it, there should be five more updates on the four other men of Blair Waldorf's life._

Daniel Humphrey: Level 1

Dan didn't love Blair Waldorf, he never had. He actually didn't even like her and sometimes he hated her, but there was a time before Serena, and before the end of sophomore year when she ascended to the role of Queen and became calculating and cruel, that Dan Humphrey had had a brief infatuation with Blair Waldorf.

They had been twelve. Blair was just a doe-eyed brunette that was best known for who she was friends with rather than for herself. She had just started dating Nate Archibald, the golden buy of the Upper East Side, and maybe that had been why his interest had been peeked with the petite beauty. There was something that happened the day everyone found out Blair Waldorf was for a lack of a better term was 'going steady' with Nate. All the girls grew jealous of Blair. All of the sudden boys who'd always been preoccupied with Serena grew envious of Nate for dating Blair; they began to desire her for themselves. Dan had been one of those boys to a much lesser extent.

He had noticed her before, it was hard not to when she and Serena Van der Woodsen were inseparable, and everyone noticed Serena. Even walking in the bubbly blonde's shadow Blair had a way about her. It was calm and regal. Back then she wasn't the manipulative bitch that had sent away Dan's sister. She wasn't an angel; he knew that. She was still elitist, a snob, and yes even then she knew how to make people do what ever she wanted, but their had been an air of innocent sweetness to her; a naïveté that had captivated him for a brief time. Back then her curls weren't always perfect behind her signature headband. Her blouse wasn't buttoned to the top, and she didn't glare when she walked. She looked approachable and nice back then when Dan had cultivated a small crush on the far away brunette. He talked to Blair, long before he'd ever spoken to Serena at that fateful party. It was the only time he hadn't seen her linking arms with Serena or holding hands with Nate or whispering with Chuck Bass, who even at twelve had a dark and dangerous reputation about him.

Dan had gone into the library during lunch to get the only copy of a book that was far beyond his years, but caught his attention like no other. He approached the old, senile librarian.

"I wanted to read the collection of poems by Alexander Pushkin, but I can't find it." He said in his most polite voice.

"If it's not on the shelf then someone must have already borrowed it. I'm sorry Daniel." The librarian knew him by name because he so often spent his lunch break in here. Dan sighed and began to walk away.

"Who at this school would possibly be reading that book?" He asked himself aloud.

"Me." Came a soft voice beside him. He turned over and saw her, the beautiful brunette. Blair hadn't even looked up from the book as she addressed him. She had a pensive look on her face.

"You're reading the collection of poems by one of the greatest Russian writers in history?" Dan asked skeptically

"I believe I already said I was. Dan, right? If you find yourself constantly stating the obvious are you sure _you_ should be reading these poems? They might go over your head." She said in a haughty tone.

"I was reading them yesterday." Dan said sitting across from her.

"And I'm reading them today, I left my copy at home."

"What are you even doing in the library? Don't you have a posse to join?"

"Posse? God you're weird. Why I'm in here is none of your business. We can't all live in this musty room because no one likes us." Her comment stung him and he furrowed his brow at her. "Sorry." She said after taking in his expression. "You caught me on a bad day."

"What happened?" He asked even though he knew he had no right to, but she fascinated him.

"Not that it's any of your business…but who are you going to tell. I'm in here because I'm currently without a single ally at this school." H cracked a smile at how she used 'ally' instead of 'friend'. "I'm glad my misfortune amuses you." Blair huffed.

"I'm sorry its just… you talk weird."

"By weird do you mean educated and mature?"

"Yes, that's exactly what I mean. Indubitably." He mocked. "But come on, I've seen you around, you have like a hundred friends."

"Those girls aren't my friends. Their just Serena's hanger-ons."

"Well what about Serena?"

"What about her? She is no longer my friend, and neither is Chuck."

"What about Nate?"

"I dumped him." Dan felt bad about how he perked up at this news, but he'd talked to Nate a few times. The guy was a moron, Blair was way to smart to waist her time with a guy like him.

"Why'd you dump him?"

"I dumped him and dismissed the rest of them because today is my birthday and not one of them remembered." She pouted.

"I'm sorry. Happy Birthday!" Dan offered weakly. Blair rolled her eyes at him. "Really, I am sorry. That sucks."

"Whatever, its fine. I can make new friends and find a new boyfriend." Dan bit back his tongue before he offered himself.

"You know Blair, you're really nice actually. I bet a ton of guys would totally want to be your…" Dan was cut off when Nate Archibald appeared at his side. Nate Archibald was tall and chiseled at twelve. He had sandy blonde hair and blue eyes that made every girl swoon over him, Blair Waldorf especially; except this time. This time she refused to even meet his gaze. Blair crossed her arms over her chest, turned her head the opposite direction of Nate and pouted petulantly.

"Blair, come one will you just talk to me." Nate pleaded.

"No." Was her quick and angry response.

" Look just listen. We didn't forget your birthday ok. We were pretending." Blair continued to ignore him. "We're throwing you a surprise party tonight, you can ask Dorota, she helped us plan it. Please don't be mad." Nate continued completely oblivious to Dan's presence. Blair turned to Nate meeting his gaze hesitantly.

"Really? You planned me a party?" Blair asked. The corners of her mouth pulled up into a small smile.

"Well technically Serena, Dorota, my mom and your dad planned it, but I helped invite everyone."

"That's so sweet." Blair said standing up to hug him.

"So you don't hate me?" Nate asked as he pulled her in closer.

"Of course not. I was being silly." Blair responded.

"So we're not broken up?" Nate asked hopefully.

"I guess not, but you better have bought me a really good present." Blair warned playfully. "I have to go forgive Serena."

"Good, she's in the bathroom crying. She totally thinks you hate her."

"Oh I better get over there quick." Blair turned toward Dan who had been listening to the whole interaction very uncomfortably. "Thanks for being so nice to me Dan. I should go."

"Wait." Nate said before pulling Blair into a kiss that was a little to long to be appropriate in public. He soon released her, and Blair Waldorf; the Upper East Side princess disappeared from the library. Nate turned to Dan finally acknowledging his existence. "Oh, hey dude. It was Dan right?"

"Yeah."

"Thanks for keeping my girl company. Blair can be a little dramatic sometimes."

"No problem."

"Ok, cool. Look I'd invite you tonight as like a thank you, but it's a sit down dinner thing and all the places and stuff are taken."

"I understand. Its cool, we just talked for a little bit."

"Well thanks again for doing that."

"Really, its fine. It was my pleasure." Nate seemed to pickup on Dan's interest in Blair from his word choice. It was funny, Dan hadn't pegged Nate for the observant type, but in the beginning of Blair and Nate's relationship Nate had been very aware, and very jealous of almost every boy that talked to Blair. Except for the one boy he really should have been watching that is.

"Well lets hope not too much of a pleasure." Nate said in a threatening tone. "We're back together, you heard her."

"Yeah I did. I didn't mean anything by it."

"Good, so I shouldn't see you sniffing around my girlfriend anytime soon. Or ever." Nate warned.

"Of course not." Dan responded, he hated how he completely backed down to Nate, but come on the guy was huge for his age and on like four sports teams.

"Then we're good." Nate smiled light-heartedly. "Later." Nate strolled out of the library; this was the first and only time he'd ever be in one.

Dan got up from his seat and picked up the book he had originally come in search of. He skimmed across the page she had been reading. It was opened to his favorite poem, "How Sweet It is…". He read the last three lines of the poem, the parallelism not lost on the bright young boy.

_**O, fairy, why… why have I seen you ever? –**_

_**Had known you, I got the Heavens bliss**_

_**And cursed my Eden in the flaming fervor.**_


	2. Chapter 2

Carter Baizen: Level 2

Carter Baizen never loved Blair Waldorf, but he did fancy her for quite sometime. Now to be clear, Carter did love Serena for a brief and fleeting period before the whole mess with the Buckleys happened. Serena was beautiful, sweet, and made him want to be a better man, but there was something missing with Serena. She lacked that killer instinct that Carter had. Blair Waldorf had that instinct, she could be manipulative and self-serving and completely spoiled, but Carter found these qualities somewhat endearing, most likely because they so closely mirrored his own. So it was only natural that Carter had always been drawn to the pouty brunette. There was a lot of speculation about why he hooked up with her when he came into town, there where three reasons really. The most obvious was she was hot, really hot and after he slept with her the first time he couldn't get enough. She was amazing in the sack, a quality Carter truly did appreciate.

The second reason Carter picked Blair was to screw with Chuck Bass. He knew it was wrong and messed up, but Chuck Bass could be such an asshole. And if Chuck was going to be a big enough dumbass to not lock that girl down then he deserved to get messed with.

Finally, and this was not only the main reason for Carter going after Blair, but also the most secret reason. The reason Carter couldn't help, but comfort the broken girl who sat dejectedly alone at the bar was simply to satisfy the boy Carter used to be. Carter was technically a man when he met Blair Waldorf the first time, at least by New York laws of consent he was, but that never stopped him with Serena. The reason Blair Waldorf had alluded him was because of Carter's protégé Nathaniel Archibald. The day he met the young brunette is a little hazy in his memory, but he still remembers almost every detail. Blair Waldorf left an impression.

Carter was eighteen and had just flunked out of Dartmouth after less than a semester. Carter returned to the city, and after the verbal lashing of a lifetime, Carter felt he'd earned the right to a stiff drink, a strong joint and entertaining company. That's how Carter ended up in Chuck Bass's suite, a newly formed freshman Carter had mentored last year along with Nate. The three boys downed tequila shots as Chuck relayed stories of his most recent conquests that brought pride to Carter. He'd trained the young boy well. Carter was on his fifth shot when a light knock came on the door. Chuck frowned as he handed his recently lit joint to Nate and went over to the door. Carter was pulled out of his haze when a tiny brunette walked into the suite. Her long curls cascaded down her back gracefully; she had on the shortest plaid skirt (one that could rival Serena's) and white knee-highs. She had that whole innocent schoolgirl thing going on, what was Carter to do? Not hit on her? She walked into the room purposely. Nate was the first to speak after trying to hide the joint Chuck had handed him.

"Nate I didn't know you'd be here." She said sweetly, her voice was soft. Carter wondered how it would sound moaning his name.

"Didn't you come here to see me?" Nate asked confused.

"Actually, I have some business to discuss with Chuck." Carter raised his eyebrow at that.

"What's the problem now Waldorf?" Chuck asked as he went to stand next to her.

"Its that bitch Georgina. Her antics no longer amuse me; she needs to go. I was hoping you could help me get rid of your little whore." Carter chuckled at the girl's vicious tone.

"Don't call her that." Chuck reprimanded. "She's not my little whore, she's the world's little whore."

"God knows she's been with enough men to constitute that title, but I do need her gone by the end of the week."

"What exactly did she do to get your La Perlas in a twist?" Chuck leered.

"We can discuss that privately, it's not something we should bore your guests with." Blair said motioning to Carter.

"Oh it seems I lost my manners…" Chuck said before being cut off.

"Like you ever had any." Blair interjected with a flip of her chestnut curls.

"This is Carter Baizen, he's an old friend from last year." Chuck continued unphased by Blair's insult.

"Nice to meet you." Carter sat up and extended his hand to the beautiful girl.

"Blair Waldorf, I've heard about you." She didn't care to elaborate, and Carter knew not to ask. She shook his hand with her soft dainty one. Blair turned to Nate. "My parents invited you to dinner to night, I'd like you to come if you're feeling up to it." She eyed his blood shoot eyes skeptically.

"Yeah sure no problem." Nate said straitening his tie.

"Blair, I believe we have plans to devise." Chuck motioned to a separate room. She nodded and began to follow him.

She stopped before entering the room. "Carter, it was nice to meet you."

"Same here." Carter responded before winking at her. She just rolled her eyes and proceeded into the room.

"Blair Waldorf, that wouldn't happen to be the Blair you've been dating since the seventh grade now would it?" Carter asked Nate.

"Yep, that's her. She's cute right?"

"She's fucking hot. Have you hit that yet?" Nate seemed to grow angry at how Carter spoke about his girlfriend.

"She wants to wait." Nate said eyeing Carter suspiciously.

"Till when, your third year anniversary?"

"Till she's ready, and I respect that."

"Oh come on, after everything I've taught you. You need to get in there and seal the deal before she finds someone else with better game and a bigger trust fund."

"Blair's not like that. She loves me."

"Every girl is like that, and love is a myth. Look don't think for a second just because you two have been dating since you were in diapers that you two are meant to be. That girl is prime real estate and I'm pretty sure there isn't a guy at St. Judes who isn't looking to remove that chastity belt of hers."

"You think?"

"I know." Nate looked off into the distance thinking over Carter's words. Carter liked Nate; the kid deserved to finally sleep with his girlfriend, but if Nate couldn't get the job done Carter would be happy to apply for the position. He actually had several positions in mind.

The next time Carter saw Blair Waldorf was at a party he threw at his penthouse later that week. He had only recently heard of her split from Nate. The two had gotten into a fight the very night he had first met Blair, when Nate showed up to dinner stoned. Needless to say World War III broke out and the two hadn't spoken since. Carter hadn't expected her to show up at the party with Serena, it didn't really seem like the uppity socialite's scene, but there she was in a short black dress nursing a martini. Nate and Chuck were off somewhere getting high and Serena was already drunk, Carter felt it was his duty to keep the girl company.

"Hello Beautiful." He greeted her.

"Carter." Blair nodded in his direction.

"I didn't expect to see you here."

"Serena brought me, I hope that's ok."

"Of course, I'd never deny a gorgeous girl entrance to my party." Blair blushed at the compliment.

"Well…your place is beautiful."

"My mom has great taste, you know if you like this room you should see the balcony. An amazing view." Blair held out her dainty hand to him.

"Show me." She said her soft voice tinkling with innocence. If it was possible she looked even prettier in the moonlight. "You were right this view is spectacular."

"Not as good as this view." Carter said looking intently at Blair.

"I don't think Nate would appreciate you hitting on me."

"Do you care what your ex thinks?"

"No." She answered with a coy smile. Carter ran his finger up and down Blair's arm. "Carter." Blair said in a warning tone.

"Come on, I know you're not naïve enough to think I brought you out here just for the view." Carter gently turned her head to his before dropping down to capture her lips. She didn't respond at first until Carter cupped her face with one hand, his other caressing her waist. She began to respond with soft, gentle kisses. Carter was about to deepen the kiss when the balcony door swung open.

"What the hell!" Nate yelled as he took in the site. Blair immediately moved out of Carter's grasp.

"Nate listen…" Carter began to explain before he was cut off by the sharp smack of Blair's hand against his cheek.

"Perv." Blair said indignantly to him. "I'm so sorry Nate, he just sprung himself on me. Please forgive me." Blair said, tears glistening in her eyes as she ran over to Nate's awaiting arms.

"Its ok Blair, I know you'd never do anything like this on purpose." Nate said soothingly as tears rolled down her creamy white cheeks. Nate turned to Carter glaring, "Stay the hell away from her. I mean it, Carter!"

Carter couldn't believe it; she had been into it, right? What the hell was going on? Nate turned to go in, Blair trailing behind him. She turned to look at Carter, all of the sudden the tears had stopped and her pout turned up into that calculating smirk he'd seen when she was plotting against Georgina at Chuck's. She raised her eyebrow at him before going inside. He couldn't believe it; she had used him. He didn't get used; he was the user. He knew he should be furious, but he found himself oddly turned on by this side of Blair.

Everyone was leaving around three a.m. as Carter sat in the corner with his scotch. He couldn't get the image of dark curls and pouty red lips out of his head.

"Don't worry, Nate will totally forgive you. He's never been very good with grudges. I'm sure a couple joints from now he'll go back to worshipping the ground you walk on." Carter turned to look at her.

"I didn't realize Nate was dating a sociopath."

"I prefer to the term truthfully challenged. Come on it was just a little slap, you can't seriously be that mad." Blair said resting her hand on his forearm.

"I suppose you could make it up to me."

"In your dreams Carter."

"Don't worry, it will be."

"I should go, Nate's downstairs with the car."

"So you made up."

"Yes, I decided it was time to forgive him, and your little P.D.A. made him all too eager to prove his worth. I'll have him call you tomorrow to make up." Blair strolled out of his apartment her head held high with victory. Carter did have to admit the view he got watching her walk away almost entirely made up for her slapping him. Nate was going to have his hands full with her.

So in the end it was really the last reason that led to Carter finding it impossible to not go over to Blair that night at the bar. Her curls weren't as perfect as the last time he'd seen her at the tea he'd attended. Her eyes were soft and sad as she starred at her martini.

"Hey beautiful." He said as he slid next to her feeling like he was eighteen again.

"What are you doing here?" She asked half-heartedly.

"I had some things to take care of in the city, but I'm doing here at this bar specifically is buying you another drink, you look like you could use one."

"Very astute."

"What happened darling?" Carter asked his hand moving to her knee, he was surprised when she didn't slap it away.

"My whole future has gone up in flames. I have nothing and no one." She answered downing the rest of her drink.

"Well if you're looking for some company…" Carter let the sentence trail off in the night.

"What are you offering exactly?"

"A couple hours of escape from the misery that is life." Blair got up abruptly, Carter's hand falling down into empty space. She walked to the door, but stopped before leaving.

"Well are you coming or not?" She asked as she looked at him with those big brown eyes. Carter's lips fell into an easy smirk as he got up and opened the door for her. Tonight he would finally get what he'd wondered about and craved since he saw her in Chuck Bass's suite. No, Carter Baizen had never loved Blair Waldorf, but he had longed for her for a very long time and the wait had been completely worth it.


	3. Chapter 3

Jack Bass- Level 3

Jack Bass wasn't sure what he felt for Blair Waldorf. She was so…complicated. Even when she was eight years old she still was able to screw with his head. That had been the first time he'd met the feisty brunette.

It had been at an Easter Party at the Van der Bilt Estate. Bart had recently brokered a deal with William, the current patriarch of the family. Bart had made him go, it was painfully boring. Everyone there was either married or six, not the twenty-three year old business grad's idea of a good time. He had stood by himself at the punchbowl unable to stand the boring business drawl, nor the squeaky chatter of the hordes of children. As he sipped his scotch and soda, a determined little girl bounded toward him. Her hair hung in soft curls behind a baby pink headband that matched her lacey pink dress. Her cheeks were rosy from running around with the other kids. He couldn't help, but think she looked like one of those porcelain dolls his grandmother had collected. She stopped in front of him and shot him a dazzling smile.

"You're Jack right?" She asked in a surprisingly assertive voice.

"Uh…yeah, I am."

"Ok good! Everyone is going to play tag and I have to tell all the kids."

She said looking up at him.

"So?" Jack answered confused by the little girl.

"Do you want to play?" She asked as if it was obvious, talking down to him.

"No. I'm not playing tag, I'm not a child." Jack answered, feeling embarrassed that he was defending himself to a kid.

"That's not what Mr. Bass says." She countered challengingly.

"What exactly did _Mr. Bass_ say?"

"I over heard him talking to Serena's mom. He said that you're just a child that dresses like an adult."

"He did, did he?"

"Yeah, he said you threw a tantrum when he said he was sending you to Australia."

"Oh yeah. Well Bart can go f…nothing. Go back to you're little friends."

"So does that mean you don't want to play?"

"No, I don't." Jack answered angrily.

"Fine." The girl answered stamping her tiny foot on the ground. Just then a much taller blonde girl came running up to the brown-haired one.

"Blair! Blair! You're mom left with a headache so you're dad sad we can do cart wheels!"

"But Serena, I already invited everyone to play tag." Blair said petulantly.

"Who cares! Carter Wheels!" Serena chirped excitedly grabbing Blair's wrist and dragging her off to the grassy knoll. Jack watched Blair begin to tumble around in the grass staining her dress. He rolled his eyes; she had gone from a bossy little girl acting like an adult, to just another simple kid.

Blair had grown up a lot by the next time he saw her, but her ability to switch personalities in the blink of an eye was still evident.

She had wanted him New Year's night. She had kissed him passionately and for one night he had had her, but the cold light of day came all too soon and then she was begging him to find Chuck. He hadn't even known until that point that she had been with Chuck. All the society gossip he had heard in the past was about her and that dopey Nathaniel Archibald, but somewhere along the way this perfect creature had fallen for his deeply screwed up nephew. He'd felt sorry for her, so he went off and searched every whorehouse in Thailand until he found Chuck strung out beyond belief. Chuck didn't deserve Blair, but he kept his promise to the doe-eyed brunette and he'd brought Chuck home.

Then Chuck had to screw everything up and try to take Bass industries away from him, after everything he'd done for Chuck! Well, that meant war, so he had taken away The Empire. He knew bringing out Evelyn to screw with him was a little much, but Chuck was such a prick. But then he got bored with Chuck's petty attempts to get his hotel back so Jack decided he'd give it back, but not until he got in one last dig. That was where Blair came in. Chuck had seemed to love Blair as much as The Empire, maybe more. That was what Jack wanted to find out. When he proposed the deal to Chuck he'd never imagined Chuck would agree, but when he did Jack's game plan changed.

He thought he'd take Blair one last time before he told her of Chuck's betrayal, but she had so clearly not been into it. She was wasted on Chuck, it was so sad. Jack did take some sick comfort in telling her how Chuck had traded her like property. Treated her like a common whore. Her pain had eased his rejection, but his heart did tear a bit when her eyes began to brim with tears and her bottom lip began to quiver.

He hadn't seen her since, but that image of her standing there in front of him, all her fire stripped away. She stood there raw and broken as her heart began to break apart in front of him. He'd hated himself that night, and whenever the image played in his head, he hated himself all over again. Love wasn't the right word for what he felt to Blair, but it wasn't entirely off. He had cared about her as much as a man like himself could care for anyone, even though he refused to admit it aloud.


End file.
